Synthesis and Characterization of Polyester Dendrimers from Acetoacetate and Acrylate

Hirayama, Yuuki; Nakamura, Taisuke; Uehara, Satoshi; Sakamoto, Yohko; Yamaguchi, Kentaro; Sei, Yoshihisa; Iwamura, Michiko

doi:10.1021/ol0482184

Cited by 16 publications

(10 citation statements)

References 15 publications

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“…43 Twibanire et al synthesized tribranched dendrons in order to prepare polyester dendrimers with denser layers than those derived from bis-HMPA and, therefore, more resistant under physiological conditions. 21g The synthesis of polyester dendrimers using as starting materials benzyl acetoacetate and tertbutyl acrylate (Figure 3c) were presented by Hirayama et al 44 Similar dendrimers, also designed to be applied as drug delivery vectors, were prepared from 3-hydroxyacetophenone and its tertbutyldimethylsilyl ether. 45 Polyester dendrimers containing tertiary amines were prepared by Bouillon et al 46 The amine groups can serve as buffers to neutralize the protons delivered from the ester hydrolysis; therefore, these poly(ester amine) dendrimers are very attractive as drug delivery vectors (Figure 3d).…”

Section: Biodegradable Dendritic Structuresmentioning

confidence: 99%

The Present and the Future of Degradable Dendrimers and Derivatives in Theranostics

Leiro¹,

Garcia²,

Tomás

et al. 2015

Bioconjugate Chem.

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Interest in dendrimer-based nanomedicines has been growing recently, as it is possible to precisely manipulate the molecular weight, chemical composition, and surface functionality of dendrimers, tuning their properties according to the desired biomedical application. However, one important concern about dendrimer-based therapeutics remains-the nondegradability under physiological conditions of the most commonly used dendrimers. Therefore, biodegradable dendrimers represent an attractive class of nanomaterials, since they present advantages over conventional nondegradable dendrimers regarding the release of the loaded molecules and the prevention of bioaccumulation of synthetic materials and subsequent cytotoxicity. Here, we present an overview of the state-of-the-art of the design of biodegradable dendritic structures, with particular focus on the hurdles regarding the use of these as vectors of drugs and nucleic acids, as well as macromolecular contrast agents.

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Section: Biodegradable Dendritic Structuresmentioning

confidence: 99%

The Present and the Future of Degradable Dendrimers and Derivatives in Theranostics

Leiro¹,

Garcia²,

Tomás

et al. 2015

Bioconjugate Chem.

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“…On the other hand, double Michael addition of acrylate derivatives has rarely been reported. Iwamura and coworkers18, 19 reported the double Michael addition of acrylates possessing large ester alkyl group with benzyl acetoacetate catalyzed by potassium hydroxide or potassium tert ‐butoxide.…”

Section: Introductionmentioning

confidence: 99%

Novel anionic polyaddition of 2‐trifluoromethylacrylate by double Michael reaction with ethyl cyanoacetate

Umino

Nozaki

Hamana

et al. 2009

J. Polym. Sci. A Polym. Chem.

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Novel fluorinated polymer synthesis with anionic polyaddition by double Michael addition reaction of 2‐trifluoromethylacrylate derivatives with ethyl cyanoacetate (ECA) was proposed. Diaddition product of ECA with phenyl 2‐trifluoromethylacrylate was yielded in high yield by the catalysis of sodium ethoxide in tetrahydrofuran at 60 °C. Sodium hydroxide catalyzed double Michael addition reaction also produced diaddition product in high yield. Novel anionic polyaddition of 1,4‐phenylene bis(2‐trifluoromethylacrylate) [CH2C(CF3)COOC6H4OCOC(CF3)CH2] (PBFA) with ECA afforded the polymer of 1.2 × 104 as the highest molecular weight. The isolated polymer gave the polymer of 2.8 × 104 as a molecular weight by the reaction of the isolated polymer with PBFA in the presence of sodium ethoxide; which proved that the polymer end groups were mainly ECA moieties. The reaction mechanism that the proton abstraction from ECA followed by the addition of 2trifluoromethylacrylate was proposed. The reaction of acetylacetone with PBFA was also examined to give the polymer of 7.6 × 103 as the highest molecular weight catalyzed by sodium hydroxide at room temperature. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 5698–5708, 2009

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“…[6][7][8][9][10][11][12][13] Defect free dendritic structures (dendrons or dendritic wedges are structurally monomolecular or unimolecular in composition) are available by the using the limited number of reactions under controlled reaction conditions of temperature, pressure, and large excess of reagents. [14][15][16][17] In the case of general polymer it is well known that every chain reaction provides a mixture of molecular linear polymers.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Unequivocal Identification of Chromophores-Substituted Carbosilane Dendrimers up to 7^thGenerations

Kim

Kim²,

Oh³

et al. 2009

Bulletin of the Korean Chemical Society

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Bis(phenylethynyl)dimethylsilane is branched by the hydrosilation of the phenylethynyl group with dichloromethylsilane, and then the resulting chlorosilane is reacted with lithium phenylacetylide to give the 1 st generation. The same hydrosilation and alkynylation are repeated to obtain the 7 th generation. In addition peripheral Si-Cl moiety of the seven kind generation dendrimers are reacted with alcoholic moiety of 9-hydroxymethylanthracene and 2-(2-hydroxyphenyl)benzoxazole group in the presence of TMEDA. Then three kinds of carbosilane dendrimers are prepared from the 1 st to the 7 th generations, the 7 th generation of each dendrimer has 256 phenylethynyl, 256 9-anthracenylmethoxy, or 128 2-(2-phenoxy)benzoxazole groups. Each synthesized dendrimer is unequivocally characterized by 1 H and 13 C NMR, elemental analysis, MALDI-MS, GPC, and PL (photoluminescence). Characteristically PDI (Polydisperse Index) values of the dendrimers' peak in GPC are in the range of 1.00~1.07, which indicates that each generation of carbosilane is in unified distribution. PL spectra of phenylethynyl and 9-anthracenemethoxy group substituted dendrimers show no significant change with increasing the generation from the 1 st to the 7 th . However, the PL spectra of 2-(2-phenoxy)benzoxazole group substituted dendrimers show a blue-shift trend with increasing the generation from the 1 st to the 7 th .

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Synthesis and Characterization of Polyester Dendrimers from Acetoacetate and Acrylate

Cited by 16 publications

References 15 publications

The Present and the Future of Degradable Dendrimers and Derivatives in Theranostics

The Present and the Future of Degradable Dendrimers and Derivatives in Theranostics

Novel anionic polyaddition of 2‐trifluoromethylacrylate by double Michael reaction with ethyl cyanoacetate

Preparation and Unequivocal Identification of Chromophores-Substituted Carbosilane Dendrimers up to 7^thGenerations

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Synthesis and Characterization of Polyester Dendrimers from Acetoacetate and Acrylate

Cited by 16 publications

References 15 publications

The Present and the Future of Degradable Dendrimers and Derivatives in Theranostics

The Present and the Future of Degradable Dendrimers and Derivatives in Theranostics

Novel anionic polyaddition of 2‐trifluoromethylacrylate by double Michael reaction with ethyl cyanoacetate

Preparation and Unequivocal Identification of Chromophores-Substituted Carbosilane Dendrimers up to 7thGenerations

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Preparation and Unequivocal Identification of Chromophores-Substituted Carbosilane Dendrimers up to 7^thGenerations